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In the title compound, [Fe(C10H8N2)3](C9H5N4O)2·2H2O, the chiral cations lie across twofold rotation axes in the space group C2/c. The anions and the water mol­ecules are linked by two independent O—H...N hydrogen bonds to form C22(8) chains, and these chains are linked by the cations via C—H...N and C—H...O hydrogen bonds to form two inter­penetrating three-dimensional frameworks, each of which contains only one enanti­omeric form of the chiral cation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614008092/yf3061sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614008092/yf3061Isup2.hkl
Contains datablock I

CCDC reference: 996644

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Tris(2,2'-bipyridine)iron(II) bis(1,1,3,3-tetracyano-2-ethoxypropenide) dihydrate top
Crystal data top
[Fe(C10H8N2)3](C9H5N4O)2·2H2OF(000) = 1928
Mr = 930.77Dx = 1.366 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9124 reflections
a = 20.273 (4) Åθ = 3.3–34.8°
b = 12.4463 (6) ŵ = 0.40 mm1
c = 19.4907 (16) ÅT = 150 K
β = 113.080 (9)°Block, red
V = 4524.3 (9) Å30.16 × 0.10 × 0.05 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
5991 independent reflections
Radiation source: fine-focus sealed tube4305 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
φ & ω scansθmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2724
Tmin = 0.842, Tmax = 0.981k = 1616
17754 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0494P)2 + 3.4815P]
where P = (Fo2 + 2Fc2)/3
5991 reflections(Δ/σ)max = 0.001
304 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.45 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.50000.63612 (4)0.75000.01652 (13)
N110.43186 (10)0.64656 (16)0.64498 (11)0.0198 (4)
C120.44707 (12)0.72318 (19)0.60388 (13)0.0209 (5)
C130.40172 (14)0.7440 (2)0.53006 (14)0.0279 (6)
H130.41400.79720.50210.033*
C140.33899 (13)0.6865 (2)0.49812 (14)0.0294 (6)
H140.30690.70050.44820.035*
C150.32346 (13)0.6082 (2)0.53967 (14)0.0297 (6)
H150.28070.56720.51860.036*
C160.37092 (13)0.5900 (2)0.61239 (14)0.0260 (6)
H160.36000.53540.64040.031*
N210.54926 (10)0.74922 (16)0.71649 (11)0.0202 (4)
C220.51385 (12)0.7822 (2)0.64485 (13)0.0213 (5)
C230.53931 (14)0.8649 (2)0.61423 (15)0.0304 (6)
H230.51340.88660.56410.037*
C240.60281 (14)0.9153 (2)0.65759 (16)0.0332 (6)
H240.62090.97260.63790.040*
C250.63942 (14)0.8809 (2)0.72990 (16)0.0326 (6)
H250.68370.91330.76030.039*
C260.61112 (13)0.7992 (2)0.75755 (15)0.0274 (6)
H260.63630.77710.80780.033*
N310.55029 (10)0.51615 (16)0.72530 (10)0.0192 (4)
C320.52812 (12)0.4162 (2)0.73492 (12)0.0198 (5)
C330.55661 (13)0.3240 (2)0.71713 (14)0.0256 (6)
H330.53980.25520.72410.031*
C340.60933 (14)0.3325 (2)0.68938 (15)0.0306 (6)
H340.62880.27030.67620.037*
C350.63307 (13)0.4337 (2)0.68120 (14)0.0292 (6)
H350.67010.44190.66330.035*
C360.60264 (13)0.5230 (2)0.69927 (14)0.0246 (6)
H360.61940.59210.69310.030*
C410.29850 (14)0.7499 (2)0.11874 (14)0.0279 (6)
C420.35522 (13)0.7675 (2)0.09577 (14)0.0277 (6)
C430.38757 (14)0.8649 (2)0.09320 (14)0.0306 (6)
C4110.26362 (14)0.6494 (2)0.10597 (15)0.0319 (6)
N4110.23421 (14)0.5681 (2)0.09626 (15)0.0423 (6)
C4120.27632 (14)0.8256 (2)0.15939 (16)0.0336 (7)
N4120.25669 (15)0.8829 (2)0.19377 (16)0.0490 (7)
O4210.38154 (10)0.67546 (15)0.07861 (11)0.0320 (4)
C4210.38097 (15)0.6646 (2)0.00419 (15)0.0328 (7)
H42A0.38180.73640.01730.039*
H42B0.33700.62670.02870.039*
C4220.44608 (15)0.6018 (3)0.01022 (16)0.0372 (7)
H42C0.44630.53260.03440.056*
H42D0.48930.64230.04000.056*
H42E0.44520.58930.03980.056*
C4310.45341 (16)0.8685 (2)0.08320 (15)0.0325 (6)
N4310.50640 (14)0.8706 (2)0.07531 (14)0.0407 (6)
C4320.35529 (15)0.9663 (2)0.09688 (15)0.0336 (7)
N4320.32946 (14)1.0475 (2)0.09803 (14)0.0444 (7)
O1W0.27576 (16)0.8453 (2)0.34988 (16)0.0719 (8)
H1A0.26520.86010.29460.108*
H1B0.27920.92160.36860.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0155 (2)0.0166 (2)0.0175 (2)0.0000.00660 (17)0.000
N110.0195 (10)0.0186 (11)0.0227 (9)0.0007 (8)0.0098 (8)0.0005 (8)
C120.0232 (12)0.0187 (13)0.0224 (11)0.0009 (9)0.0106 (9)0.0008 (10)
C130.0317 (14)0.0304 (15)0.0233 (12)0.0002 (11)0.0125 (10)0.0044 (11)
C140.0263 (13)0.0384 (16)0.0188 (12)0.0045 (11)0.0039 (10)0.0011 (11)
C150.0212 (13)0.0354 (16)0.0273 (13)0.0058 (10)0.0037 (10)0.0023 (11)
C160.0220 (12)0.0292 (14)0.0242 (12)0.0048 (10)0.0063 (10)0.0006 (11)
N210.0191 (10)0.0204 (11)0.0237 (10)0.0035 (8)0.0111 (8)0.0029 (8)
C220.0218 (12)0.0222 (13)0.0235 (12)0.0000 (9)0.0129 (10)0.0019 (10)
C230.0327 (14)0.0308 (15)0.0309 (13)0.0023 (12)0.0158 (11)0.0046 (12)
C240.0359 (15)0.0270 (16)0.0456 (17)0.0067 (12)0.0256 (13)0.0027 (13)
C250.0296 (14)0.0319 (17)0.0390 (15)0.0118 (11)0.0166 (12)0.0091 (13)
C260.0236 (13)0.0308 (15)0.0283 (13)0.0046 (10)0.0108 (10)0.0034 (11)
N310.0165 (9)0.0233 (11)0.0164 (9)0.0001 (8)0.0049 (7)0.0015 (8)
C320.0192 (11)0.0206 (13)0.0153 (10)0.0011 (9)0.0020 (9)0.0006 (9)
C330.0274 (13)0.0224 (13)0.0240 (12)0.0022 (10)0.0069 (10)0.0022 (10)
C340.0323 (14)0.0284 (15)0.0283 (13)0.0112 (11)0.0089 (11)0.0065 (11)
C350.0221 (13)0.0385 (16)0.0289 (13)0.0050 (11)0.0120 (10)0.0062 (12)
C360.0208 (12)0.0286 (15)0.0252 (12)0.0012 (10)0.0097 (10)0.0029 (11)
C410.0266 (13)0.0309 (15)0.0255 (13)0.0098 (11)0.0094 (10)0.0001 (11)
C420.0280 (14)0.0316 (16)0.0212 (12)0.0136 (11)0.0073 (10)0.0041 (11)
C430.0367 (15)0.0294 (15)0.0243 (12)0.0098 (12)0.0103 (11)0.0033 (12)
C4110.0309 (14)0.0361 (18)0.0337 (14)0.0121 (12)0.0181 (11)0.0016 (13)
N4110.0415 (15)0.0421 (17)0.0533 (16)0.0046 (12)0.0293 (12)0.0022 (13)
C4120.0285 (14)0.0407 (17)0.0313 (14)0.0078 (12)0.0115 (11)0.0004 (13)
N4120.0537 (17)0.0511 (19)0.0526 (17)0.0065 (13)0.0320 (14)0.0113 (14)
O4210.0390 (11)0.0284 (10)0.0362 (10)0.0148 (8)0.0229 (9)0.0049 (9)
C4210.0348 (15)0.0347 (17)0.0249 (13)0.0064 (11)0.0073 (11)0.0050 (12)
C4220.0374 (16)0.0439 (19)0.0344 (15)0.0101 (13)0.0185 (12)0.0034 (13)
C4310.0419 (16)0.0264 (15)0.0259 (13)0.0037 (12)0.0097 (11)0.0032 (12)
N4310.0456 (15)0.0380 (15)0.0426 (14)0.0037 (12)0.0218 (12)0.0023 (12)
C4320.0392 (16)0.0348 (17)0.0223 (13)0.0068 (13)0.0074 (11)0.0021 (12)
N4320.0554 (16)0.0350 (16)0.0346 (13)0.0173 (12)0.0090 (12)0.0008 (12)
O1W0.095 (2)0.0594 (19)0.0708 (18)0.0148 (15)0.0428 (16)0.0088 (14)
Geometric parameters (Å, º) top
Fe1—N111.9744 (19)C32—C32i1.473 (5)
Fe1—N11i1.9744 (19)C32—C331.389 (3)
Fe1—N21i1.979 (2)C33—H330.9500
Fe1—N211.979 (2)C33—C341.378 (4)
Fe1—N311.971 (2)C34—H340.9500
Fe1—N31i1.971 (2)C34—C351.379 (4)
N11—C121.356 (3)C35—H350.9500
N11—C161.345 (3)C35—C361.382 (4)
C12—C131.395 (3)C36—H360.9500
C12—C221.470 (3)C41—C421.405 (4)
C13—H130.9500C41—C4111.411 (4)
C13—C141.377 (4)C41—C4121.413 (4)
C14—H140.9500C42—C431.388 (4)
C14—C151.380 (4)C42—O4211.360 (3)
C15—H150.9500C43—C4311.423 (4)
C15—C161.384 (3)C43—C4321.436 (4)
C16—H160.9500C411—N4111.151 (4)
N21—C221.359 (3)C412—N4121.151 (4)
N21—C261.347 (3)O421—C4211.452 (3)
C22—C231.387 (4)C421—H42A0.9900
C23—H230.9500C421—H42B0.9900
C23—C241.383 (4)C421—C4221.499 (4)
C24—H240.9500C422—H42C0.9800
C24—C251.378 (4)C422—H42D0.9800
C25—H250.9500C422—H42E0.9800
C25—C261.377 (4)C431—N4311.144 (4)
C26—H260.9500C432—N4321.142 (4)
N31—C321.360 (3)O1W—H1A1.0292
N31—C361.347 (3)O1W—H1B1.0099
N11—Fe1—N11i172.46 (12)N21—C26—C25122.8 (2)
N11i—Fe1—N2193.27 (8)N21—C26—H26118.6
N11—Fe1—N21i93.26 (8)C25—C26—H26118.6
N11i—Fe1—N21i81.35 (8)C32—N31—Fe1115.38 (16)
N11—Fe1—N2181.35 (8)C36—N31—Fe1127.14 (17)
N21—Fe1—N21i89.33 (12)C36—N31—C32117.5 (2)
N31—Fe1—N1190.87 (8)N31—C32—C32i113.83 (14)
N31i—Fe1—N11i90.87 (8)N31—C32—C33122.0 (2)
N31i—Fe1—N1194.84 (8)C33—C32—C32i124.21 (16)
N31—Fe1—N11i94.84 (8)C32—C33—H33120.1
N31—Fe1—N2194.70 (8)C34—C33—C32119.8 (3)
N31—Fe1—N21i174.62 (8)C34—C33—H33120.1
N31i—Fe1—N21174.62 (8)C33—C34—H34120.8
N31i—Fe1—N21i94.70 (8)C33—C34—C35118.4 (2)
N31—Fe1—N31i81.50 (12)C35—C34—H34120.8
C12—N11—Fe1115.46 (15)C34—C35—H35120.2
C16—N11—Fe1126.50 (17)C34—C35—C36119.6 (3)
C16—N11—C12117.9 (2)C36—C35—H35120.2
N11—C12—C13122.0 (2)N31—C36—C35122.8 (3)
N11—C12—C22113.9 (2)N31—C36—H36118.6
C13—C12—C22124.2 (2)C35—C36—H36118.6
C12—C13—H13120.4C42—C41—C411119.9 (2)
C14—C13—C12119.2 (2)C42—C41—C412123.7 (3)
C14—C13—H13120.4C411—C41—C412116.3 (3)
C13—C14—H14120.5C43—C42—C41127.2 (2)
C13—C14—C15119.0 (2)O421—C42—C41113.3 (2)
C15—C14—H14120.5O421—C42—C43119.4 (2)
C14—C15—H15120.4C42—C43—C431121.0 (3)
C14—C15—C16119.3 (2)C42—C43—C432122.3 (3)
C16—C15—H15120.4C431—C43—C432116.7 (3)
N11—C16—C15122.6 (2)N411—C411—C41178.5 (3)
N11—C16—H16118.7N412—C412—C41176.4 (4)
C15—C16—H16118.7C42—O421—C421118.3 (2)
C22—N21—Fe1114.96 (15)O421—C421—H42A110.1
C26—N21—Fe1127.25 (17)O421—C421—H42B110.1
C26—N21—C22117.7 (2)O421—C421—C422108.0 (2)
N21—C22—C12114.2 (2)H42A—C421—H42B108.4
N21—C22—C23122.0 (2)C422—C421—H42A110.1
C23—C22—C12123.8 (2)C422—C421—H42B110.1
C22—C23—H23120.4C421—C422—H42C109.5
C24—C23—C22119.2 (2)C421—C422—H42D109.5
C24—C23—H23120.4C421—C422—H42E109.5
C23—C24—H24120.5H42C—C422—H42D109.5
C25—C24—C23118.9 (3)H42C—C422—H42E109.5
C25—C24—H24120.5H42D—C422—H42E109.5
C24—C25—H25120.4N431—C431—C43179.5 (3)
C26—C25—C24119.3 (2)N432—C432—C43178.3 (3)
C26—C25—H25120.4H1A—O1W—H1B99.5
Fe1—N11—C12—C13176.4 (2)N21—Fe1—N31—C363.60 (19)
Fe1—N11—C12—C222.3 (3)N21—C22—C23—C240.3 (4)
Fe1—N11—C16—C15175.1 (2)C22—C12—C13—C14177.4 (2)
Fe1—N21—C22—C123.3 (3)C22—N21—C26—C250.2 (4)
Fe1—N21—C22—C23176.4 (2)C22—C23—C24—C250.7 (4)
Fe1—N21—C26—C25176.8 (2)C23—C24—C25—C261.4 (4)
Fe1—N31—C32—C32i2.2 (3)C24—C25—C26—N211.2 (4)
Fe1—N31—C32—C33177.50 (17)C26—N21—C22—C12179.7 (2)
Fe1—N31—C36—C35177.79 (18)C26—N21—C22—C230.6 (4)
N11—Fe1—N21—C223.54 (17)N31—Fe1—N11—C1297.82 (18)
N11i—Fe1—N21—C22171.15 (17)N31i—Fe1—N11—C12179.37 (17)
N11—Fe1—N21—C26179.8 (2)N31i—Fe1—N11—C164.6 (2)
N11i—Fe1—N21—C265.5 (2)N31—Fe1—N11—C1686.2 (2)
N11i—Fe1—N31—C3291.00 (16)N31—Fe1—N21—C2293.71 (17)
N11—Fe1—N31—C3293.92 (16)N31—Fe1—N21—C2689.7 (2)
N11—Fe1—N31—C3684.99 (19)N31i—Fe1—N31—C320.84 (11)
N11i—Fe1—N31—C3690.1 (2)N31i—Fe1—N31—C36179.8 (2)
N11—C12—C13—C141.1 (4)N31—C32—C33—C340.5 (3)
N11—C12—C22—N210.6 (3)C32—N31—C36—C351.1 (3)
N11—C12—C22—C23179.1 (2)C32i—C32—C33—C34179.8 (3)
C12—N11—C16—C150.9 (4)C32—C33—C34—C351.0 (4)
C12—C13—C14—C151.3 (4)C33—C34—C35—C361.4 (4)
C12—C22—C23—C24180.0 (2)C34—C35—C36—N310.4 (4)
C13—C12—C22—N21179.3 (2)C36—N31—C32—C32i178.7 (2)
C13—C12—C22—C230.4 (4)C36—N31—C32—C331.5 (3)
C13—C14—C15—C160.5 (4)C41—C42—C43—C431167.2 (2)
C14—C15—C16—N110.6 (4)C41—C42—C43—C43215.7 (4)
C16—N11—C12—C130.0 (4)C41—C42—O421—C421122.0 (2)
C16—N11—C12—C22178.7 (2)C42—O421—C421—C422145.8 (2)
N21i—Fe1—N11—C1285.63 (18)C43—C42—C41—C411169.1 (2)
N21—Fe1—N11—C123.20 (17)C43—C42—C41—C41215.5 (4)
N21—Fe1—N11—C16179.2 (2)C43—C42—O421—C42161.3 (3)
N21i—Fe1—N11—C1690.4 (2)C411—C41—C42—O42114.6 (3)
N21i—Fe1—N21—C2289.86 (17)C412—C41—C42—O421160.8 (2)
N21i—Fe1—N21—C2686.8 (2)O421—C42—C43—C4318.9 (4)
N21—Fe1—N31—C32175.31 (16)O421—C42—C43—C432168.2 (2)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg1 represents the centroid of the N11/C12–C16 ring.
D—H···AD—HH···AD···AD—H···A
C14—H14···O1W0.952.523.316 (4)141
C15—H15···N432ii0.952.503.296 (4)142
C23—H23···N431iii0.952.593.439 (4)148
C26—H26···Cg1i0.952.913.697 (3)141
O1W—H1A···N4121.031.932.950 (4)173
O1W—H1B···N411iv1.012.003.000 (4)169
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+1/2, y1/2, z+1/2; (iii) x+1, y, z+1/2; (iv) x+1/2, y+1/2, z+1/2.
 

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